How to Turn a Hook-Up Into a Friend With Benefits

Damn, why’s it so hard for a girl to find a fuckbuddy around here?! A lot of paid dating sites are relationship-focused, while the free hookup sites that are actually free focus primarily on one-off fucks. There’s not a lot of recourse for those of us who want something in the middle: a reliable and enduring connection, without the potentially draining heaviness of a new romantic relationship. Where do you even go to look for a sweet and dedicated fuckpal these days?

Back when I was actively trawling Tinder on the regs, often my “holy grail” was the hope of turning a one-night stand into a FWB. I viewed these low-stakes dates as “auditions” and sought chemistry I thought could translate into something more lasting. And I indeed picked up some terrific bang-buddies in the process, so I guess I know what I’m talking about. Here are my best tips for morphing a fuck into a fuck-friend…

Be upfront about what you want. Some people treat Tinder as essentially Grindr for straight people (…or gay people or bi people or pan people or whatever the case may be) and make it clear that they’re only looking for one night of magic, not an ongoing connection. Since that’s pretty much the norm, you have to make your intentions clear if that’s not where you’re at. Even something brief like “ideally looking for a FWB situation” in your bio can attract the right kinds of people while scaring off the ones who want something else.

Showcase your awesome personality. For me, the difference between someone I want to bone once and someone I want to keep boning is primarily how I feel about just hanging out with them when we’re not having sex. If I can’t stand their brain, why would I wanna keep fucking their body? By that same token, someone smart and hilarious will definitely creep up my “dream FWBs” list faster than a boring clod. So don’t turn into a sex-focused cyborg: let that sparkling personality shine!

Give a shit about your partner’s pleasure. One-night stands aren’t exactly known for conjuring the heights of ecstasy. It’s tough to get to know someone’s body well enough that quickly to really knock their socks off. But if you demonstrate a passion for pleasing, you’re likelier to get a callback. You may be on the hunt for something casual, but that doesn’t mean you get to slack off in the sexual generosity department!

Appeal to their kinks and fantasies, and share yours. Granted, not everybody gets into a sexual psychology discussion on the first (or only) date, but if you do, remember what they tell you! If they’re a burgeoning sadist, secret submissive, or humiliation glutton, you may not be able to work that stuff into a first-time bang sesh, but it could give you material for future sexting and lascivious invitations. Sexual chemistry isn’t just about how your bodies fit together – it’s also about how well your fantasies mesh, and to what extent you’re able to stimulate each other’s minds. Hinting at compatibility in this area can make you seem like a more alluring FWB.

Make them an offer they can’t refuse. Okay, they can still refuse it, obviously, ’cause consent. But inviting your hookup to an event – like a theme night at a local sex club – can be a cool way to follow up after a one-night encounter. You could also invite them over for a particular sexual purpose: “I’m craving that cock in my mouth again,” for example, or “I’m curious about those rope bondage skills you mentioned last time.” The specificity of these offers makes them more appealing, and easier to say “yes” to, than something more nebulous like “Wanna hang out again sometime?” Enough of these repeat encounters and you might just parlay your one-off into an ongoing thing.

Have you ever transformed a one-night stand into an open-ended copulationship? How did you go about it?

 

This post was sponsored. As always, all writing and opinions are my own.

A Tale of Three Blowjobs: Getting Over Penis Terror, Continued

My very first post on this blog was about something I termed “penis terror.” Maybe that doesn’t bode especially well as a kick-off to a sex blog… but at the time, it was the main sexual issue occupying my mind.

See, when I was a youngin (by which I mean age 15–18), penises – and men in general – made me very, very nervous. I had a plethora of anxieties and neuroses about male sexuality. I believed men were hard-wired to be sexually aggressive, to put their own sexual desires above women’s, and to judge women’s sexual performance against impossible pornographic standards. And that shit terrified me.

It’s so embarrassing and strange to recount this now, but in my first sexual relationship with a cis guy, I literally cried the first several times his penis was brought up in sexual conversation. I was so fucking nervous and I can’t even explicitly identify, in retrospect, what was making me so nervous. It was just a fear of the unknown, I guess.

I worried I would be bad at pleasing penises, and that my boyfriend would judge me or leave me for it; I worried that touching penises would somehow make me “slutty” or “tainted,” even though I intellectually knew these are bullshit concepts; and, maybe most frighteningly of all, I worried I wouldn’t like penises. I was petrified that I’d turn out to be biromantic but homosexual – because I knew I wanted to date and kiss and cuddle with men most of the time, but I didn’t know if I also wanted to fuck them. And that was a scary, dicey question hanging in the air.

 

But my feelings about penises have transformed monumentally over the years. I crave them, I appreciate them, I write them love songs and gratitude missives. They’re kind of one of my favorite things.

There’s no clearer barometer of my penis-comfort than my attitude about performing oral sex on them. So, for your amusement: a tale of three blowjobs.

 

1.

My journal entry for July 5th, 2011 begins: “Today will go down in history as the first time I ever put a penis in my mouth.” A tad dramatic, perhaps, but it really did feel that significant to me.

I was nineteen years old. My very non-scientific Twitter poll indicates that this makes me a relatively late bloomer. What can I say? Willies gave me the willies. But when I did finally get around to it (with some very gentle prompting from my then-boyfriend), it wasn’t anywhere near as bad as I thought it was going to be.

Granted, he didn’t come in my mouth that first time, which definitely made it easier to handle. But, overall, I considered it a huge step forward and an even huger relief. I had a major fear reference; I felt invincible.

“Throughout all of this penis stuff,” I wrote in my journal, “I have learned that there are two things I need in order to comfortably jump into a fear: a supportive, loving, respectful environment, and a little push.”

 

2.

After the aforementioned First Penis In My Mouth (and its owner) exited my life, I started to wonder if the same fears would rear their head again when I got another dude into my bed.

I broke a long dry spell by romancing a cute guy from the internet. During the proceedings, he very politely asked if I’d go down on him, and I immediately did, and it was good.

It wasn’t until a couple days later that it occurred to me: Huh. What took me literal months of waffling and wailing with my first serious boyfriend only took one respectful request with a hook-up. I guess I really am over that fear at long last.

The one fellatio-related anxiety that lingered for me, though, was being watched while going down. Maybe it’s linked to my fanaticism over blowjob porn and some shitty internalized ideas about “sluttiness,” or maybe it’s just insecurity about the way I look, but I’ve always hated being watched while giving a BJ.

I explained this to Adorable Internet Hook-up and he seemed to have no problem with it whatsoever. We turned off the light and all was fine and good. But, well, you hear a lot of things about how the visual of a BJ is almost as important for men as the actual sensations. Obviously preferences vary from person to person, but as someone who loves watching, say, Heather Harmon inhale a dick, I totally get the appeal. And I was bummed I still couldn’t be looked at while my mouth was full of cock.

 

3.

Shortly thereafter, I had sex with a… uh, how do I even put this? A friend who I also now like to kiss and have sex with? (Um, obviously I am new to this whole sex-outside-of-relationships thing, but, semantic difficulties aside, it is fucking great.)

When a blowjob became imminent, he grabbed his glasses off the nightstand where he had set them during our makeouts. I asked him what he was doing and he said, “I want to watch.”

For some reason I didn’t even think twice about this. I guess I was preoccupied by the prospect of a cock in my mouth. (Cocks!!!) As before, it took a day or two for my brain to properly process the magnitude of what had happened. I had let someone watch me blow him! And this had previously been one of my biggest sexual insecurities!

As we were putting our clothes back on afterward and getting ready to leave, the guy even said to me that he thought I’d look hot giving him a beej on my knees, and instead of reacting with terror, I just giggled with delight. Because, yes, this is a thing that I would like to do…

 

Did you have any anxieties or insecurities to deal with when you first started giving oral sex? How did you overcome them?